Last Updated: September 17, 2020 

Dateline: Hong Kong

Ever since I first came to Hong Kong, I’ve been in love with the place. The city is bustling, the weather is perfect, and the scenery is a mix of urban chaos and an odd sense of Asian calmness. 

On top of that, Hong Kong has some of the world’s best restaurants, amazing shopping, and – even despite the recent social unrest – one of the most stable banking and business jurisdictions on the planet. 

But I’m going to let you in on a little secret: I couldn’t stand staying here that long.

It’s not because one of my companies is based in Hong Kong and my living here would cost me more money. And it’s not because of the living expenses. (Even though it took me weeks to find an apartment as large, well-located, and luxurious as the one I had in Kuala Lumpur… and the rent was $42,000 a month.)

The reason I couldn’t spend my entire life in Hong Kong — or even a significant period of time — is because doing so would ruin it.

There’s something magical about Hong Kong in the way that there’s something magical about Las Vegas.

When I was a young kid starting my business in Arizona (and briefly in Southern California), I often frequented Vegas for business and leisure – or “bleisure” as the cool kids are calling it now. Driving over the mountain and seeing the lights of the Las Vegas Strip was as exciting the 25th time as it was the first.

However, whenever I would talk to a group of European guys at a craps table or Middle Eastern girls in the lobby, I was astounded when they would tell me they were visiting for two whole weeks.

What the hell is there to do in Las Vegas for TWO WEEKS? The magic wears off in a few days! It’s best to leave after a long weekend, just soon enough to want to come back and do it all over again.

Now, I don’t spend time in Las Vegas these days — Macau is far cooler for the more mature me — but I do understand that the Nomad Capitalist lifestyle is one that must be adapted to the person living it.

For some people, that means living a life of nothing but proverbial visits to Las Vegas, where you leave just as soon as the magic wears off.

For others, that means finding a new home in one of my New Safe Havens and settling down in a permanent home there in traditional expat style.

For others still, it’s something in between.

Whenever I hear people talk about the nomad lifestyle or perpetual travelers, I often hear certain stereotypes thrown around. For example, even when I was visiting 25 countries a year in my most nomadic days, people assumed that I didn’t have a home of my own and merely lived in hotels.

Likewise, someone might assume that a digital nomad bounces from Airbnb to Airbnb, and co-working space to co-working space.

But that’s not always true.

I started out as a young guy with a business, living in the United States, and wanting to travel. I began with one trip and then quickly got up to many trips in a year. Before I knew it, I was traveling more than I was at home.

Soon enough, I left the United States for good to become a full-time perpetual traveler, dragging an oversized Tumi bag behind me.

Now, however, I have settled down to the point that I have places that I call home, places that I feel at home in, and places that I am still exploring. 

Each of these parts of my Nomad lifestyle fits into my overall strategy and goals to not only explore the world but also find new opportunities and make investments.

With these years of experience, I’ve come up with four different ways to live a Nomad Capitalist lifestyle. 

These four strategies present different ways you can live your life based on how much time you want to spend in any given place, how much time you like being away from home, and whether you want a home at all. 

I’m open to hearing your ideas if you have more and would like to add on to what I’ve observed.


Ready? Let’s take a look at the four strategies for living a Nomad lifestyle:


This is the Nomad lifestyle many digital nomads pursue. It’s how I lived once I started spending my entire life on the road. The perpetual traveler has no permanent address and no permanent home, choosing instead to live life out of a suitcase.

For example, I spent the second half of 2013 traversing most of Southeast Asia, making connections, and investigating deals in each country. In order to do that, I gave myself one month in most countries, which I eventually shortened to 2-3 weeks. I started in Vietnam and continued to Cambodia, Thailand, Laos, Malaysia, Indonesia, and then the Philippines.

Then, the first half of 2014 was spent in Eastern Europe, starting in the Baltics and working my way down to the Balkans at a slightly faster pace.

I spent years doing this. I spent almost every day at a hotel. I literally had a couple of different suitcases and I was very limited in what I could take with me – I had to be very careful, especially because I was meeting bank presidents and other professionals. 

I had to pack suits and nice shoes, but I also needed to pack casual clothing. Things I couldn’t fit in my suitcase, I had to get rid of or donate. It was a bit of a challenge to live a totally nomadic lifestyle. 

There is no perfect strategy for being a perpetual traveler. The system I used back then could work as well with shorter trips, or with more extended trips.

For example, several friends of mine commit to three months in each city, giving them plenty of time to get accustomed to their surroundings. Most of the freelancers I collaborated with back in the day through Hubstaff (a well-recommended platform we used for hiring talented remote workers before opting for a more permanent team) chose to live like this.

To me, such a long stay doesn’t really feel like I’m a “perpetual traveler”, but rather an expat with several homes. That said, if you bounce from one Airbnb apartment or hotel room to the next with nowhere to leave your belongings, that counts.

On the other hand, some PTs and digital nomads bounce from place to place at lightning speed; I believe my record was 30 countries in one year.

Pros of being a perpetual traveler:
  • It’s a great way to try on different cities before committing to a more permanent strategy
  • You get to experience more places
  • It can be part of a global investment strategy
Cons of being a perpetual traveler:
  • It’s easier to get lonely, and you’ll have a harder time maintaining relationships with people you meet there
  • It’s hard to fit everything you need in a suitcase
  • Having no permanent address may make it harder to open a bank account, establish a tax residence, or start a company


The more time I spent away from my home country, the more I craved a base. I did the full-on perpetual traveler Nomad lifestyle routine, but my penchant for decorating and the fact that I own a lot of suits and carry-on luggage means that I prefer to have a base these days.

This strategy provides a good balance. You get the benefits of traveling and the stability of having places to call home (and to keep the stuff you can’t fit in your suitcase). 

My first base was Kuala Lumpur, Malaysia – one of my favorite cities in the world (read my recommendations for living in KL) where I have based myself for many years. 

It is a great base, especially because it gives you access to two airlines that fly everywhere very affordably, plus quick access to Singapore for even more options. KL is also a great base because you can bank and store your assets in neighboring Singapore while living in the more interesting and cost-effective Malaysia.

However, having one foreign base can start to look a lot like being a traditional expat if you don’t travel much. That’s where the idea of multiple bases comes into play.

Since first writing this article, I have perfected this method of living, dubbing it my Trifecta Strategy.

There are many benefits of this approach to the Nomad lifestyle. First off, it can be helpful from a tax-planning standpoint because you’re not going to be spending enough time in any one location to qualify as a tax resident. 

Tax residence is a little more complicated than simply spending less than half the year in any one location. There are a lot of nuances to establishing (or avoiding) tax residence. But in theory, the Trifecta can be a good way to plan for taxes. 

But tax benefits or not, the second benefit is that the Trifecta Strategy gives you a taste all the things you enjoy about different parts of the world. 

Personally, I like the food and culture in Latin America, I like the modern 21st-century feel and the hustle and bustle buzz of Asia, and I love the charm of Europe. 

With the Trifecta Strategy, I have a base that feeds each one of these urges. 

And instead of staying in a hotel or an Airbnb and dragging a suitcase behind me everywhere I go, I can walk into my home and there are my phone charger and toothbrush. I don´t have to go searching through my bags. They are right where I need them to be. Plus, there is art on the walls and season-appropriate clothing in the closet. 

It’s all ready to go and tailored to my exact tastes and needs.

Langkawi Malaaysia Ways to Live a Nomad Lifestyle

Whether you want beaches with lighthouses or snowy mountains, there is a way to get a little bit of everything with the Trifecta Nomad lifestyle.

The Trifecta Strategy is the perpetual traveler strategy meets a stable home base with settled housing arrangements.

And best of all, you can have as many homes as you want. A gentleman recently came to me and said he wanted six homes where he could spend two months per year in each unique location. You can do that!

There are endless possibilities for how you could set up your own personal Trifecta Strategy.

Perhaps you never want to deal with winter. Or maybe you’re like me and just can’t sit still. When I’m in Asia, I start wondering about what’s going on in Europe, and vice versa. 

So, let’s take a look at some examples of this Nomad strategy:

Example #1:

You love the warm weather and opportunities in Asia, but you miss Europe from time to time and love the quiet summers there. 

In this case, you could rent an apartment in Singapore and own a home in Belgrade – my Balkan base city

Both cities are well-connected, so it’s easy to travel back and forth. It’s also easy to travel around the region when you have business trips or want a weekend off.

Example #2:

You’re a lifestyle real estate investor who likes owning different types of properties. 

Perhaps you buy a condo in the sky in Kuala Lumpur, a beach apartment in Montenegro, a house with a yard in Panama, and your original home in the city you left to do all this traveling. 

You could easily bounce between all of your properties, always having a place in each part of the world to call home without having to stay in a hotel.

Example #3:

You’re a true nomad who wants to be connected to all three major parts of the world: the Americas, Europe, and Asia. You could buy homes in Medellin, Colombia and Malta, then rent a place in Bangkok. 

Medellin has food and culture, Malta has relaxation and access to the rest of Europe, and Bangkok has the hustle and bustle and start-up culture

You move around as you see fit.

The list of possibilities is endless. Of course, base cities give you access to more regional travel. For example, I’ve had bases in Malaysia, Montenegro, Georgia, Colombia, Serbia, and Belgium. From there, I’ve easily been able to get anywhere I want without hassles.

Tbilisi isn’t the best-connected city, but it is close enough to get around Eastern Europe, including borderline-frontier markets like Ukraine or Armenia. 

Northern Belgium is small enough that it’s easy to get to Brussels airport (or Amsterdam or Paris) from anywhere by train, and from there to anywhere in the world. And KL can get you anywhere in Asia, Australia, or Europe.

This is my current personal strategy; I like the flexibility of being able to have several homes set up the way I want. I love feeling at home without having to stay at the often-dreadfully decorated short-term rentals in the countries I visit.

The Trifecta Strategy also allows you to enjoy a lifestyle buffet: the big city, the small town, the beach, and whatever else it is you’re after. And if you choose your countries carefully, you can get second residence permits and eventually passports just for buying property

Pros of the base cities strategy:
  • Your life is less stressful as you have each home set up the way you want it
  • You can manage parts of your business, or multiple businesses, in each place
  • You can travel between multiple homes for business or leisure without wondering what to expect
  • You can manage a real estate portfolio around the world for your own benefit
Cons of the base cities strategy:
  • You have multiple properties to maintain and, if you rent, leases to pay even when you don’t live there
  • You might feel pressured to spend more time in one of your homes “because it’s there”
  • Owning properties in multiple places can blur the distinction between a home to live in and an investment


This strategy is similar to the Trifecta Strategy, but it involves one base and a number of “focus cities”. In case you’re not familiar with the term, focus cities are what airlines call the cities they serve with great frequency, but that aren’t full-fledged hubs.

This strategy is for someone who wants a home but also wants the perpetual traveler lifestyle without the surprises. It’s perfect for someone with less cash to invest or cash to spend every month on rent.

Here’s how it works: you have a home in one base city that acts as your personal hub. This is where you keep all of your stuff and the place from which you travel. However, unlike a traditional expat, you have a list of cities that you know well enough to feel at home in.

While you don’t have a technical base of operations in your focus cities, you know how to get around, know where the best restaurants are, know where to get your dry cleaning done, and know how to get back to the airport without wasting time. 

You feel at home without having a home there.

Then, you simply determine how long you want to spend in each focus city, or group of focus cities, before returning to base. You’ll never deal with the feeling of new-ness in a city.

The benefit of having focus cities is that you can develop habits there. For example, I’ve been to Singapore enough times that I know exactly where I want to stay depending on my spending preference that trip. I know where to eat and how to get around. 

Most importantly, not only do I know people there that I can call and meet, but there are other people and businesses I would like to get to know.

A focus city can also be a city where you hold assets, have bank accounts, or have other flags planted. After dozens of trips to Hong Kong and Singapore, I feel extremely comfortable in both; partially because I’ve made the mental connection of having part of my assets there.

I have also set up my team in three strategic locations that have become additional focus cities, giving me a greater reason to visit each one to do training and work in-person with different teams.

Building your list of focus cities takes time, so this is a strategy that is best used by recovering perpetual travelers, or people who are willing to visit a rotation of cities frequently enough to get used to them. 

It took me almost a decade to develop my list of focus city candidates: Dublin, Warsaw, Brussels, Riga, Tbilisi, Istanbul, Panama City, Belgrade, Yerevan, Hong Kong, Singapore, and Phnom Penh. 

Maybe I’m missing a few.

Pros of the Base + Travel strategy:
  • You will always feel at home without the discomforts of being in an unfamiliar place
  • You can visit focus cities without ever getting bored of being there
  • It’s a great excuse to check up on banks, assets, or employees in a fun way
Cons of the Base + Travel strategy:
  • You don’t get the benefits of storing your stuff in another city, which could make longer trips difficult
  • You still have the costs of living like a tourist, which in cities like Singapore, could be expensive


Expat Nomad Lifestyle

If you’re ready to call somewhere home and settle down, the expat Nomad lifestyle may be right for you.

The expat lifestyle is the opposite end of the spectrum from the perpetual traveler. A lot of people assume that I’m only talking about being an expat when I talk about being a Nomad Capitalist, but that isn’t always the case. 

Being an expat is pretty straightforward: you settle down in one city in a country different than where you’re from. Many expats settle in financial hubs like Dubai, Hong Kong, or Singapore. 

While this way of living doesn’t particularly suit me (at least yet), for some reason it tends to be shunned by many in the Nomad community as being boring.

The funny thing is that, while traveling and living overseas is supposed to be all about breaking the rules and living life your way, some people fall into the same rut of “follow the leader” and, instead of living life their way, they only attempt to replicate the same nothing-but-a-suitcase lifestyle they see others living.

It’s your life. If you want to live as an expat, you should do it, regardless of how “awesomesauce” some digital nomad blog says perpetual travel is. 

Being an expat doesn’t mean you’ll never leave your new city; the same way you aren’t tied down to the city where you currently live. You can be an expat and travel, too.

Being a full-time expat is best suited to families or those who want the stability of one place most of the year. Expats can still travel on summer vacation, or take trips whenever they please, of course. It just means that they tend to make simple, Point A – Point B – Point A trips that return them home.

Pros of the expat strategy:
  • Having one permanent address makes opening bank accounts, starting companies, and obtaining travel visas much easier
  • Spending a longer time in one country may qualify you for a second residence or second citizenship
  • You may feel comfortable if you’re used to living in and traveling from one place, particularly if you are a family with children
  • You will have greater opportunities to connect to the local community and build friendships
Cons of the expat strategy:
  • Living in one place for most of the year may subject you to tax, depending on the country
  • You may get bored if you’re used to adventure

Design Your Personal Nomad Lifestyle

As you can see, there are many different ways you can live the Nomad lifestyle. There are also many spinoffs you could take from any one of these strategies. 

You could decide that you don’t want the full Trifecta but are happy establishing a summer home and a winter home. Or, maybe you set up the six bases my client decided he wanted.

If you can run your business from anywhere, you can have two bases or six bases or expand it even more. You can make it whatever you want it to be.

What I really want to impart is that there is no right or wrong way to do this. 

Obviously, a lot of people we talk to here at Nomad Capitalist like the idea of arranging their life so that they can pay less in taxes and keep more of their own money, and this is possible with any of these strategies depending on your overall setup.

You can also use any of these different strategies to get second passports through investment or naturalization. And flag-planting aside, you can use these Nomad lifestyle design tips to simply improve your life and live how and where you’re treated best.

I live my life a certain way, but you can live any one of these ways or a variation of them and still accomplish a lot of the goals we talk about: more money, more freedom, more opportunities.

If you want help setting up your own Nomad lifestyle and offshore strategy, feel free to reach out to our team. It is our mission to help you go where you’re treated best, wherever and however that might be.

Andrew Henderson
Last updated: Sep 17, 2020 at 9:20AM